Multi-step reaction with 17 steps
1.1: n-butyllithium / tetrahydrofuran / 0.75 h / -78 °C
1.2: 3.5 h / 0 - 20 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C
2.2: -78 °C
2.3: 16 h / -78 - 27 °C
3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C
4.1: hydrogen; palladium 10% on activated carbon / water / 3 h / 20 °C / 760.05 Torr
5.1: acetic acid; hydrogen bromide / 4 h / Reflux
6.1: acetyl chloride / 4 h / 0 °C / Reflux
7.1: sodium hydrogencarbonate / methanol; water / 3 h / 0 - 20 °C
8.1: pyridine / 2.5 h / 0 - 20 °C
9.1: tri-tert-butyl phosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / acetonitrile; hexane / 5 h / Inert atmosphere; Reflux
10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C
11.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / 0 °C
12.1: ammonia / methanol / 18 h / 0 - 20 °C
13.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
14.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
15.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 6 h / 20 °C
16.1: acetic acid; sodium cyanoborohydride / methanol / 19 h / 20 °C
17.1: sodium hydrogencarbonate / methanol; water / 0.17 h / 0 °C
17.2: 3 h / 0 - 20 °C
With
4-methyl-morpholine; pyridine; hydrogenchloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; tri-tert-butyl phosphine; palladium 10% on activated carbon; ammonia; water; hydrogen bromide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; triethylamine; acetyl chloride; sodium hydroxide; lithium hydroxide; isobutyl chloroformate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; acetonitrile;